Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety

Saki Yajima, Tsuyoshi Saitoh, Kohei Kawa, Kensuke Nakamura, Hiroshi Nagase, Yasuaki Einaga, Shigeru Nishiyama

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Cyclohexadienone derivatives possessing α-D-glucopyranosyl moiety were designed and synthesized using chemical oxidation or electrochemical oxidation with boron-doped diamond electrode in the final stage. In the chiral induction studies, catalytic hydrogenation provided high diastereoselectivity (dr ratio: > 9:1). Conformational analyses of the C-glucoside structures were performed by NOE experiments and force field calculations, and supported the observed regio-selectivity.

Original languageEnglish
Pages (from-to)8428-8435
Number of pages8
JournalTetrahedron
Volume72
Issue number51
DOIs
Publication statusPublished - 2016 Dec 22

Fingerprint

Diamond
Boron
Hydrogenation
Electrochemical oxidation
Glucosides
Electrodes
Derivatives
Oxidation
Experiments
cyclohexadienone

Keywords

  • Anodic oxidation
  • Boron-doped diamond electrodes
  • Cyclohexadienone
  • Diastereoselective hydrogenation
  • Hypervalent iodobenzene

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Yajima, S., Saitoh, T., Kawa, K., Nakamura, K., Nagase, H., Einaga, Y., & Nishiyama, S. (2016). Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety. Tetrahedron, 72(51), 8428-8435. https://doi.org/10.1016/j.tet.2016.10.068

Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety. / Yajima, Saki; Saitoh, Tsuyoshi; Kawa, Kohei; Nakamura, Kensuke; Nagase, Hiroshi; Einaga, Yasuaki; Nishiyama, Shigeru.

In: Tetrahedron, Vol. 72, No. 51, 22.12.2016, p. 8428-8435.

Research output: Contribution to journalArticle

Yajima, S, Saitoh, T, Kawa, K, Nakamura, K, Nagase, H, Einaga, Y & Nishiyama, S 2016, 'Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety', Tetrahedron, vol. 72, no. 51, pp. 8428-8435. https://doi.org/10.1016/j.tet.2016.10.068
Yajima, Saki ; Saitoh, Tsuyoshi ; Kawa, Kohei ; Nakamura, Kensuke ; Nagase, Hiroshi ; Einaga, Yasuaki ; Nishiyama, Shigeru. / Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety. In: Tetrahedron. 2016 ; Vol. 72, No. 51. pp. 8428-8435.
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